ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Dimethyl Sulfoxide → (3S,4S)-3-acetyl-1-(tert-butyldimethylsilyl)-4-trimethylsilylethynyl-2-azetidinone

HRID 231237
ノート
印刷プレビュー

反応式

HRID 231237 の反応式
FC(F)(F)C(O)=O.CS(C)=O.[Si:12]([N:19]1[C@H:22]([C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C@H:21]([C@H:29]([OH:31])[CH3:30])[C:20]1=[O:32])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(N(CC)CC)C>C(Cl)Cl.O.C(OCC)(=O)C>[C:29]([C@@H:21]1[C@@H:22]([C:23]#[C:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[N:19]([Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[C:20]1=[O:32])(=[O:31])[CH3:30]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 679Dimethyl SulfoxideHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 67788869cis-1-(tert-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone

生成物 1

HCID 53923801(3S,4S)-3-acetyl-1-(tert-butyldimethylsilyl)-4-trimethylsilylethynyl-2-azetidinone収率 32.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 6344Dichloromethane溶媒3 回
HCID 8857Ethyl Acetate溶媒

反応条件

温度
-70 °C

実験手順

In an argon stream, a solution of dry trifluoroacetic acid (0.2 ml) in methylene chloride (3 ml) is added dropwise to a mixture of dimethyl sulfoxide (0.1 ml) and methylene chloride (10 ml) at -65° C. or lower, and the mixture is stirred at -70° C. for 0.5 hours. A solution of cis-1-(tert-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone (0.4 g) in methylene chloride (4 ml) is added dropwise at -65° C. or lower and the mixture is stirred at the same temperature for 0.5 hour. After addition of triethylamine (0.3 ml) at the same temperature, the temperature is gradually raised to room temperature. The reaction mixture is poured into a mixture of ethyl acetate (70 ml) and water (100 ml), and the organic layer is separated, washed with aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residue is subjected to silica gel column chromatography (eluent: 3% ethyl acetate-97% n-hexane) to give trans i.e. (3S,4S)-3-acetyl-1-(tert-butyldimethylsilyl)-4-trimethylsilylethynyl-2-azetidinone (0.13 g)

後処理

  1. stirringlower and the mixture is stirred at the same temperature for 0.5 hour
  2. temperaturethe temperature is gradually raised to room temperature
  3. customthe organic layer is separated
  4. washwashed with aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-bbcc503110d94085a8f8865eb0323174
出典データセット
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04845210

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート